CN109400506B - Synthesis method of high-purity chlorosulfonyl isocyanate - Google Patents
Synthesis method of high-purity chlorosulfonyl isocyanate Download PDFInfo
- Publication number
- CN109400506B CN109400506B CN201811353003.8A CN201811353003A CN109400506B CN 109400506 B CN109400506 B CN 109400506B CN 201811353003 A CN201811353003 A CN 201811353003A CN 109400506 B CN109400506 B CN 109400506B
- Authority
- CN
- China
- Prior art keywords
- tower
- reaction
- distillation
- light component
- component removal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/06—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a synthesis method of high-purity chlorosulfonyl isocyanate, which comprises the following steps: A) in the presence of a diluent, carrying out sulfonation reaction on sulfur trioxide and chlorocyanogen to obtain a reaction solution; B) carrying out thermal decomposition reaction on the reaction liquid to obtain a thermally decomposed reaction liquid; C) carrying out positive pressure continuous distillation on the reaction liquid after thermal decomposition to obtain high-purity chlorosulfonyl isocyanate and distillation front fraction; the diluent is selected from chlorosulfonyl isocyanate or the distillation front fraction. The synthesis method provided by the invention improves the total yield of the process; the method adopts the distillate before distillation as the reaction solvent, avoids the use of a high-boiling point solvent, recovers part of the chlorocyanogen and the sulfur trioxide in the pyrolysis process, improves the utilization rate of the raw materials, and reduces the production cost. Meanwhile, the rectification process of the process is carried out in a positive pressure distillation and continuous feeding mode, so that the yield of the product is greatly improved, the distillation time is shortened, the energy consumption and the labor cost are reduced, and the process is suitable for industrial large-scale production.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of high-purity chlorosulfonyl isocyanate.
Background
Chlorosulfonyl isocyanate is a very reactive intermediate. The substance reacts with hydroxyl, amino and carboxyl to generate N-chlorosulfonylamino formate, urea and amide. Can be added with water, active hydrogen, alcohol, phenol, amine, amide, carboxylic acid, olefin, aldehyde, ketone and ester to obtain various new compounds, which can be used as dehydrating agent and oxidizing agent. The chlorosulfonyl isocyanate is mainly used for producing cefuroxime, cefoxitin, carumonam and other medicines.
The chlorosulfonyl isocyanate in industrial production is not complicated in manufacturing process, and generally, chlorocyanogen and sulfur trioxide are adopted to react, and then the crude product chlorosulfonyl isocyanate obtained by the reaction is purified and separated to obtain the product chlorosulfonyl isocyanate. The prior production method is mature, but the technical level is not high. Such as patents JP77855 and EP294613, the reaction conditions are harsh and not suitable for industrial production; CN101891657 uses inert solvent, and direct distillation, not to handle the impurity that the side reaction produced, easily cause the product purity to be lower, can not operate for a long time. Therefore, it is a technical problem to be solved to provide a synthesis method capable of improving yield and purity, and applicable to industrial production.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide a method for synthesizing chlorosulfonyl isocyanate with high purity, which has the advantages of high product yield and purity, mild reaction conditions, and easy industrialization.
The invention provides a synthesis method of high-purity chlorosulfonyl isocyanate, which comprises the following steps:
A) in the presence of a diluent, carrying out sulfonation reaction on sulfur trioxide and chlorocyanogen to obtain a reaction solution;
B) carrying out thermal decomposition reaction on the reaction liquid to obtain a thermally decomposed reaction liquid;
C) carrying out positive pressure continuous distillation on the reaction liquid after thermal decomposition to obtain high-purity chlorosulfonyl isocyanate and distillation front fraction;
the diluent is selected from chlorosulfonyl isocyanate or the distillation front fraction obtained in step C).
Firstly, carrying out sulfonation reaction on sulfur trioxide and chlorocyanogen, specifically, adding a diluent into a reaction device, then adding the sulfur trioxide and the chlorocyanogen into the reaction device to carry out the sulfonation reaction, and obtaining a reaction solution after the reaction is finished.
Wherein the diluent is selected from chlorosulfonyl isocyanate or the distillation front fraction obtained in step C). In the present invention, chlorosulfonyl isocyanate may be used as a diluent in the first batch of production of chlorosulfonyl isocyanate, and then the distillation front fraction obtained after continuous distillation using positive pressure in the subsequent batches may be used.
Wherein the usage amount of the diluent is 1-5% of the total amount of the fed materials.
Wherein the temperature of the sulfonation reaction is 28-43 ℃, preferably 30-40 ℃, and more preferably 32-38 ℃.
The molar ratio of the sulfur trioxide to the chlorocyanogen is 1: (0.8 to 1.2), preferably 1: (0.9-11).
In the present invention, the chlorocyanogen is prepared according to the following reaction equation:
Cl2+NaCN→ClCN
specifically, liquid chlorine and sodium cyanide aqueous solution are subjected to chlorination reaction in a chlorination reactor at the same time, and then pure liquid cyanogen chloride is prepared through cooling, drying and refining.
And then heating the reaction liquid to raise the temperature for carrying out thermal decomposition reaction, wherein the temperature of the thermal decomposition reaction is 100-120 ℃, and preferably 105-115 ℃. The thermal decomposition reaction is preferably carried out in a thermal decomposition apparatus, and the present invention is not particularly limited to a specific source of the thermal decomposition apparatus, and any thermal decomposition apparatus known to those skilled in the art may be used. And collecting sulfur trioxide and chlorocyanogen in the reaction process in the thermal decomposition process. After completion of the thermal decomposition, a reaction solution after the thermal decomposition was obtained.
Then, the reaction solution after the thermal decomposition is continuously distilled under positive pressure to obtain high-purity chlorosulfonyl isocyanate and a distillation front fraction.
Wherein the positive pressure continuous distillation is carried out in a continuous distillation system, see fig. 1, fig. 1 is a schematic diagram of the continuous distillation system provided by the present invention. The continuous distillation system comprises:
the device comprises a light component removing upper tower, a light component removing middle tower and a light component removing lower tower which are sequentially connected from top to bottom, wherein a feed liquid inlet is formed in the middle of the light component removing upper tower;
the heavy component removal tower is characterized in that a liquid inlet is connected with a liquid outlet of the light component removal lower tower, a distillation front fraction outlet is arranged at the upper part of the heavy component removal tower, a finished product outlet is arranged at the middle part of the heavy component removal tower, and a heavy component outlet is arranged at the lower part of the heavy component removal tower.
In some embodiments of the invention, the light ends upper column, the light ends middle column, the light ends lower column and the heavy ends lower column are packed columns. The filler is not particularly limited in the present invention, and any filler known to those skilled in the art to be usable for distillation of chlorosulfonyl isocyanate may be used.
The filler in the upper light component removing tower is arranged in a segmented manner, the filler in the upper light component removing tower is divided into an upper section filler and a lower section filler, and the feed liquid inlet is formed in the wall of the upper light component removing tower and is positioned between the upper section filler and the lower section filler.
The light component removing middle tower and the light component removing lower tower are not arranged in sections.
The liquid outlet of the upper light component removal tower is connected with the liquid inlet of the middle light component removal tower, the liquid outlet of the upper light component removal tower is arranged at the bottom end of the upper light component removal tower, and the liquid inlet of the middle light component removal tower is arranged at the upper part of the middle light component removal tower and is positioned above the filler in the middle light component removal tower.
The liquid outlet of the light component removing middle tower is connected with the liquid inlet of the light component removing lower tower, the liquid outlet of the light component removing middle tower is arranged at the bottom end of the light component removing middle tower, and the liquid inlet of the light component removing lower tower is arranged at the upper part of the light component removing lower tower and is positioned above the filler on the tower wall of the light component removing lower tower.
The packing in the heavy component removal tower is arranged in a segmented manner, and the packing in the heavy component removal tower is divided into an upper section of packing, a middle section of packing and a lower section of packing;
and the liquid inlet of the light component removal tower is arranged at the bottom end of the light component removal tower, and the liquid inlet of the heavy component removal tower is arranged on the tower wall of the heavy component removal tower and is positioned between the middle section filler and the lower section filler.
A distillation front fraction outlet is arranged at the upper part of the de-heavy tower, and in some specific embodiments of the invention, the front fraction outlet is arranged on the wall of the de-heavy tower and is positioned above the upper-section packing;
a finished product outlet is arranged in the middle of the de-weighting tower, and in some specific embodiments of the invention, the finished product outlet is arranged on the tower wall of the de-weighting tower and is positioned between the middle section filler and the lower section filler;
the heavy component outlet is arranged at the lower part of the heavy component removing tower, and in some specific embodiments of the invention, the heavy component outlet is arranged at the bottom of the heavy component removing tower.
The pressure in the continuous distillation system was 1.5 MPa.
When the positive pressure continuous distillation is carried out, the reaction liquid after thermal decomposition is continuously introduced into a continuous distillation system through a feed liquid inlet, the boiling point of the reaction liquid after thermal decomposition in the continuous distillation system reaches above 130 ℃, then the reaction liquid after thermal decomposition is completely decomposed in a light component removing upper tower and a light component removing middle tower, a nearly qualified product is obtained after the separation of the light component removing lower tower, and then the product is extracted through a lateral outlet of the light component removing lower tower and enters a heavy component removing tower for rectification to obtain the qualified product. Therefore, the current 3-4 times of repeated rectification process is reduced, and the yield and the output of the product are improved. The product is subjected to primary continuous rectification to prepare chlorosulfonyl isocyanate meeting the quality requirement, and the obtained distillation front cut fraction is reserved as a next reaction diluent.
And when the positive pressure continuous distillation is carried out, the tower top temperature of the light component removing upper tower, the light component removing middle tower, the light component removing lower tower and the heavy component removing tower is 93-100 ℃. The pressure of the positive pressure continuous distillation is 1.5-2.0 MPa.
In the prior art, the batch distillation needs two times of rough distillation and one time of rectification to obtain a qualified product, the total distillation yield is 65-70%, the kettle residue is large, the energy consumption is large, and the product purity is more than 99%.
The continuous distillation provided by the invention can obtain qualified products at one time, the total distillation yield is 90%, the residue in the kettle is small, the energy is saved, and the product purity is more than 99.5%.
Referring to fig. 2, fig. 2 is a schematic flow chart of a synthetic method of the high-purity chlorosulfonyl isocyanate provided by the invention. Namely, the sulfur trioxide and the chlorocyanogen are firstly subjected to sulfonation reaction, and then are subjected to pyrolysis and distillation in sequence to obtain the chlorosulfonyl isocyanate, wherein the distillation front cut fraction can be used as a solvent of the sulfonation reaction, and the sulfur trioxide and the chlorocyanogen collected in the pyrolysis process can be used as raw materials of the sulfonation reaction.
The reaction equation is as follows:
compared with the prior art, the invention provides a method for synthesizing high-purity chlorosulfonyl isocyanate, which comprises the following steps: A) in the presence of a diluent, carrying out sulfonation reaction on sulfur trioxide and chlorocyanogen to obtain a reaction solution; B) carrying out thermal decomposition reaction on the reaction liquid to obtain a thermally decomposed reaction liquid; C) carrying out positive pressure continuous distillation on the reaction liquid after thermal decomposition to obtain high-purity chlorosulfonyl isocyanate and distillation front fraction; the diluent is selected from chlorosulfonyl isocyanate or the distillation front fraction obtained in step C). The synthesis method provided by the invention improves the total yield of the process; the method adopts the distillate before distillation as the reaction solvent, avoids the use of a high-boiling point solvent, recovers part of the chlorocyanogen and the sulfur trioxide in the pyrolysis process, improves the utilization rate of the raw materials, and reduces the production cost. Meanwhile, the rectification process of the process is carried out in a positive pressure distillation and continuous feeding mode, so that the yield of the product is greatly improved, the distillation time is shortened, the energy consumption and the labor cost are reduced, and the process is suitable for industrial large-scale production. The method has simple operation, reduced production cost, and safe and reliable production process.
Drawings
FIG. 1 is a schematic diagram of a continuous distillation system provided by the present invention;
FIG. 2 is a schematic flow chart of a synthetic method of high-purity chlorosulfonyl isocyanate provided by the invention.
Detailed Description
For further understanding of the present invention, the synthesis method of high purity chlorosulfonyl isocyanate provided by the present invention is illustrated below with reference to the following examples, and the scope of the present invention is not limited by the following examples.
Example 1
This embodiment provides a continuous distillation system comprising:
the device comprises a light component removing upper tower, a light component removing middle tower and a light component removing lower tower which are sequentially connected from top to bottom, wherein a feed liquid inlet is formed in the middle of the light component removing upper tower;
the heavy component removal tower is characterized in that a liquid inlet is connected with a liquid outlet of the light component removal lower tower, a distillation front fraction outlet is arranged at the upper part of the heavy component removal tower, a finished product outlet is arranged at the middle part of the heavy component removal tower, and a heavy component outlet is arranged at the lower part of the heavy component removal tower.
The light component removing upper tower, the light component removing middle tower, the light component removing lower tower and the heavy component removing tower are packed towers, and the packing is selected from 700Y wire mesh corrugated packing.
The filler in the upper light component removing tower is arranged in a segmented manner, the filler in the upper light component removing tower is divided into an upper section filler and a lower section filler, and the feed liquid inlet is formed in the wall of the upper light component removing tower and is positioned between the upper section filler and the lower section filler.
The light component removing middle tower and the light component removing lower tower are not arranged in sections.
The liquid outlet of the upper light component removal tower is connected with the liquid inlet of the middle light component removal tower, the liquid outlet of the upper light component removal tower is arranged at the bottom end of the upper light component removal tower, and the liquid inlet of the middle light component removal tower is arranged at the upper part of the middle light component removal tower and is positioned above the filler in the middle light component removal tower.
The liquid outlet of the light component removing middle tower is connected with the liquid inlet of the light component removing lower tower, the liquid outlet of the light component removing middle tower is arranged at the bottom end of the light component removing middle tower, and the liquid inlet of the light component removing lower tower is arranged at the upper part of the light component removing lower tower and is positioned above the filler on the tower wall of the light component removing lower tower.
The packing in the heavy component removal tower is arranged in a segmented manner, and the packing in the heavy component removal tower is divided into an upper section of packing, a middle section of packing and a lower section of packing;
and the liquid inlet of the light component removal tower is arranged at the bottom end of the light component removal tower, and the liquid inlet of the heavy component removal tower is arranged on the tower wall of the heavy component removal tower and is positioned between the middle section filler and the lower section filler.
A distillation front fraction outlet is arranged at the upper part of the de-heavy tower, and the front fraction outlet is arranged on the wall of the de-heavy tower and is positioned above the upper section of the filler;
a finished product outlet is formed in the middle of the de-weighting tower, is formed in the tower wall of the de-weighting tower and is positioned between the middle section filler and the lower section filler;
and a heavy component outlet is formed in the lower part of the heavy component removal tower and is arranged at the bottom of the heavy component removal tower.
The pressure in the continuous distillation system is 1.5-2.0 MPa.
And when the positive pressure continuous distillation is carried out, controlling the tower top temperatures of the light component removing upper tower, the light component removing middle tower, the light component removing lower tower and the heavy component removing tower to be 93-100 ℃.
The continuous distillation system provided in example 1 was used for the continuous distillation in examples 2 to 4 below.
Example 2
20mL of chlorosulfonic acid isocyanate was charged as a reaction solvent into the reaction apparatus, and 80.06g of sulfur trioxide and 61.47g of chlorocyanogen were introduced simultaneously in a fixed amount to react while maintaining the temperature at 30 ℃. Heating the reaction solution to 120 ℃ for thermal decomposition, recovering sulfur trioxide, and introducing into the next sulfonation reaction. Rectifying the reaction liquid after thermal decomposition, wherein the reaction liquid is distilled continuously. And (3) heating the bottom of the light component removal lower tower while feeding, then heating the light component removal middle tower and the light component removal upper tower, and when the pressure in the kettle reaches 1.7Mpa and the temperature at the top of the tower reaches 95 ℃, carrying out total reflux for 2 hours, ensuring that the continuous re-feeding is carried out after the thermal decomposition is fully completed, and simultaneously continuously extracting front distillate and finished products to obtain 118.9g of chlorosulfonyl isocyanate with the purity of 99.5 percent, wherein the primary yield of the product reaches over 84 percent.
Example 3
Adding 20mL of the previous fraction into a reaction device as a reaction solvent, introducing 80.06g of sulfur trioxide, 61.47g of cyanogen chloride and a recovery gas at the same time, and keeping the temperature at 34 ℃ for reaction. Heating the reaction liquid to 100 ℃ for thermal decomposition, and recovering sulfur trioxide. Rectifying the reaction liquid after thermal decomposition, wherein the reaction liquid is distilled continuously. And (3) feeding, heating the bottom of the light-component removing lower tower, then heating the light-component removing middle tower and the light-component removing upper tower, when the pressure in the kettle reaches 1.5Mpa, the temperature at the top of the tower reaches 93 ℃, carrying out total reflux for 2 hours, ensuring that the continuous re-feeding is carried out after the thermal decomposition is fully completed, simultaneously carrying out front distillation and continuous extraction of finished products, thus obtaining 121.6g of chlorosulfonyl isocyanate with the purity of 99.5 percent, and the primary yield of the product reaches more than 86 percent.
Example 4
Adding 20mL of the previous fraction as a reaction solvent into a reaction device, introducing 80.06g of sulfur trioxide, 61.47g of cyanogen chloride and a recovery gas at the same time, and keeping the temperature at 36 ℃ for reaction. Heating the reaction liquid to 110 ℃ for thermal decomposition, and recovering sulfur trioxide. Rectifying the reaction liquid after thermal decomposition, wherein the reaction liquid is distilled continuously. And (3) heating the bottom of the light component removal lower tower while feeding, then heating the light component removal middle tower and the light component removal upper tower, when the pressure in the kettle reaches 2.0Mpa, the temperature at the top of the tower reaches 100 ℃, carrying out total reflux for 2 hours, ensuring that the continuous re-feeding is carried out after the thermal decomposition is fully completed, simultaneously carrying out front distillation and continuous extraction of finished products, and obtaining 120.9g of chlorosulfonyl isocyanate with the purity of 99.5 percent, wherein the primary yield of the product reaches more than 85 percent.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (5)
1. A method for synthesizing chlorosulfonyl isocyanate is characterized by comprising the following steps:
A) in the presence of a diluent, carrying out sulfonation reaction on sulfur trioxide and chlorocyanogen to obtain a reaction solution;
B) carrying out thermal decomposition reaction on the reaction liquid to obtain a thermally decomposed reaction liquid;
C) carrying out positive pressure continuous distillation on the reaction liquid after thermal decomposition to obtain high-purity chlorosulfonyl isocyanate and distillation front fraction;
said diluent is selected from chlorosulfonyl isocyanate or said distillation front fraction obtained in step C);
the pressure of the positive pressure continuous distillation is 1.5-2.0 MPa, and the time of the positive pressure continuous distillation is 2 hours;
the positive pressure continuous distillation is conducted in a continuous distillation system comprising:
the device comprises a light component removing upper tower, a light component removing middle tower and a light component removing lower tower which are sequentially connected from top to bottom, wherein a feed liquid inlet is formed in the middle of the light component removing upper tower;
the heavy component removal tower is characterized in that a liquid inlet is connected with a liquid outlet of the light component removal lower tower, a distillation front fraction outlet is arranged at the upper part of the heavy component removal tower, a finished product outlet is arranged at the middle part of the heavy component removal tower, and a heavy component outlet is arranged at the lower part of the heavy component removal tower.
2. The synthesis method according to claim 1, wherein the temperature of the sulfonation reaction is 28-43 ℃.
3. The synthesis process according to claim 1, characterized in that the molar ratio of sulfur trioxide to chlorocyanogen is 1: (0.8 to 1.2).
4. The synthesis method according to claim 1, wherein the temperature of the thermal decomposition reaction is 100 to 120 ℃.
5. The synthesis method according to claim 1, wherein the tower top temperature of the light component removal upper tower, the light component removal middle tower, the light component removal lower tower and the heavy component removal tower is 93-100 ℃.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811353003.8A CN109400506B (en) | 2018-11-14 | 2018-11-14 | Synthesis method of high-purity chlorosulfonyl isocyanate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811353003.8A CN109400506B (en) | 2018-11-14 | 2018-11-14 | Synthesis method of high-purity chlorosulfonyl isocyanate |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109400506A CN109400506A (en) | 2019-03-01 |
CN109400506B true CN109400506B (en) | 2021-04-13 |
Family
ID=65473124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811353003.8A Active CN109400506B (en) | 2018-11-14 | 2018-11-14 | Synthesis method of high-purity chlorosulfonyl isocyanate |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109400506B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112174860B (en) * | 2020-10-09 | 2023-10-13 | 天津昊然分离科技有限公司 | Process method for preparing chlorosulfonyl isocyanate through continuous reactive distillation |
CN112321462B (en) * | 2020-11-02 | 2023-02-24 | 四平市精细化学品有限公司 | Method for synthesizing chlorosulfonyl isocyanate by continuous method |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH330713A (en) * | 1952-03-24 | 1958-06-15 | Hoechst Ag | Process for the preparation of a nitrogen and sulfur containing compound of the formula CO6NCIS2 |
DE3719303A1 (en) * | 1987-06-10 | 1988-12-29 | Hoechst Ag | METHOD AND INSTALLATION FOR THE CONTINUOUS PRODUCTION OF CHLORSULFONYLISOCYANATE |
US5118487A (en) * | 1990-09-11 | 1992-06-02 | Kuraray Co., Ltd. | Process for producing chlorosulfonyl isocyanate |
CH680292A5 (en) * | 1990-10-04 | 1992-07-31 | Lonza Ag | Chlorosulphonyl isocyanate continuous prodn. - comprises reacting cyanogen chloride and sulphur tri:oxide in liq. prod. using heat of reaction for distn. |
JP3161723B2 (en) * | 1990-10-29 | 2001-04-25 | 株式会社クラレ | Method for producing chlorosulfonyl isocyanate |
JP2000053630A (en) * | 1998-05-14 | 2000-02-22 | Sumitomo Chem Co Ltd | Production of chlorosulfonyl isocyanate |
JP4004867B2 (en) * | 2002-06-20 | 2007-11-07 | 日本曹達株式会社 | Method for producing chlorosulfonyl isocyanate |
CN1264814C (en) * | 2003-07-04 | 2006-07-19 | 四平市精细化学品有限公司 | Method for preparing chlorine sulfonyl isocyanic ester |
WO2005058806A1 (en) * | 2003-12-16 | 2005-06-30 | Nippon Soda Co., Ltd. | Method for producing chlorosulfonyl isocyanate |
CN101891657B (en) * | 2010-07-15 | 2011-08-31 | 营口三征新科技化工有限公司 | Manufacturing method of chlorosulfonyl isocyanate |
CN104447438A (en) * | 2014-11-20 | 2015-03-25 | 沈阳化工大学 | Method for producing chlorosulfonyl isocyanate by taking cyanogen chloride and sulfur trioxide as raw materials |
-
2018
- 2018-11-14 CN CN201811353003.8A patent/CN109400506B/en active Active
Also Published As
Publication number | Publication date |
---|---|
CN109400506A (en) | 2019-03-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103130197B (en) | Continuous-pressure-changing rectification method and device for preparing medicine-level sulfoxide chloride | |
CN103880690B (en) | A kind of environment friendly clean producing method of glycine | |
CN109400506B (en) | Synthesis method of high-purity chlorosulfonyl isocyanate | |
CN114602406B (en) | Production device and production method of lithium hexafluorophosphate | |
CN103274913A (en) | Method and device for producing methyl isobutyl ketone | |
CN114456131A (en) | Tetrahydrofuran production system and preparation method | |
CN102516015A (en) | Production method and system for extracting refined anthracene and carbazole by using crystallization distillation method | |
CN101891583A (en) | Method for co-production of trichloroethylene and tetrachloroethylene by gas phase catalysis method | |
CN103950952A (en) | Preparation method of high-purity deuterated ammonia | |
CN102875371A (en) | Method for synthesizing cyclohexyl acetate from cyclohexene | |
CN101229988B (en) | Method for refining high-purity anthracene and carbazole from crude anthracene | |
CN105237428B (en) | A kind of production technology of formamide for suppressing polymer generation | |
CN104370746A (en) | Cost-saving preparation method of p-nitrobenzyl alcohol | |
CN103435508A (en) | Preparation process and device for N,N-diethylformamide | |
CN101306980B (en) | Method for preparing perchloro cyclopentadiene | |
CN114920630B (en) | Continuous production process and equipment for ethylene glycol monovinyl ether | |
CN103318958B (en) | Separation and refining method of arsenic trioxide | |
CN110156724B (en) | Device and method for preparing epoxy compound by batch reaction | |
CN210030511U (en) | Production device of dimethyl sulfone | |
CN104163761A (en) | Method for refining dimethyl succinate by rectification | |
CN110551025B (en) | System and method for recovering and refining by-product methyl formate in coal-to-ethylene glycol process | |
CN203816452U (en) | System for treating by-product exhaust generated in chloromethane production | |
CN108129321B (en) | Synthetic method of pesticide intermediate 4-formyl methyl valerate | |
CN103922892A (en) | Method for preparing 3,4-dichloro bromobenzene | |
CN109250694B (en) | Method for preparing hydroxylamine hydrochloride by using hydrogen chloride dry gas |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |